Dimethylformamide → HCID 86649315, compound

HRID 1623565Notes

Reaction equation

HRID 1623565 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][C:8]([Si:11]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:12][C@@H:13](C)[CH2:14]C(O)=O)([CH3:10])[CH3:9].CN(C=O)C>C(Cl)Cl>[CH3:7][C:8]([Si:11]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[O:12][C@@H:13]([CH3:14])[CH2:1][C:2]([Cl:4])=[O:3])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58715070HCID 58715070, compound

Product 1

HCID 86649315HCID 86649315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.1 mL, 48 mmol; conc. 1.5 g/mL) was added dropwise to a stirred solution of intermediate D2 (11 g, 32 mmol) and DMF (1 mL) in DCM (300 mL) at r.t. for 90 min. The reaction mixture was evaporated under reduced pressure and co-evaporated with toluene (×3) to give the crude intermediate D3 as a yellow oil. This material was used in the next step of the reaction sequence without any further purification.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure and co-evaporated with toluene (×3)

Sources & evidence

ORD record
ord-1ce54abd5a1b40aeb3886bd2af55d8f5
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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